Organoselenium-Catalyzed Oxidative Allylic Fluorination with Electrophilic N-F Reagent
Organoselenium-Catalyzed Oxidative Allylic Fluorination with Electrophilic N-F Reagent
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DOI：
10.1021/acscatal.7b03829
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发表时间：
2018-02-01
期刊：
影响因子：
12.9
通讯作者：
Zhao, Xiaodan
中科院分区：
文献类型：
--
作者：
Guo, Ruizhi;Huang, Jiachen;Zhao, Xiaodan
发展了一条有机硒催化氧化烯丙位醛的有效路线。在该转化中，使用大体积亲电氟化试剂N-氟-2，4，6-三甲基吡啶鎓三氟甲磺酸盐（TMFP-OTf）作为氧化剂和氟源。值得注意的是，作为添加剂的克里思会影响聚合度，并导致更好的底物范围和优异的官能团耐受性。通过该方法，以良好的产率合成了多种烯丙基氟。所得烯丙基氟在合适的碱存在下可有效地转化为氟乙烯。
An efficient route of organoselenium-catalyzed oxidative allylic fluorination has been developed. In this transformation, bulky electrophilic fluorinating reagent N-fluoro-2,4,6-trimethylpyridinium triflate (TMFP-OTf) was employed as the oxidant and fluorine source. Notably, TEMPO as an additive affects the fluorination and leads to better substrate scope and excellent functional group tolerance. By this protocol, a variety of allylic fluorides were synthesized in good to excellent yields. The obtained allylic fluorides could be converted into vinyl fluorides efficiently in the presence of an appropriate base.